Main Street of Monticello, Florida, Inc.

Here’s one of the several Bike Festivals we hold in Monticello and Jefferson County.

To see more pictures of the Bike Fest visit here

I Found it in Historic Monticello

I Found it in Historic Monticello

Upcoming Events

Downtown Christmas

Monticello’s Downtown Community Christmas Event
Friday December 1, 2017 – 5:00 pm to 8:00 pm

Presented by Main Street of Monticello

Join us for a holiday scavenger hunt and raffle!

Please join us for our Annual Downtown Community Christmas event! Spend the evening in our Historic downtown of Monticello, enjoying dinner at one of our many local restaurants, visiting the live nativity at the United Methodist Church and taking a free tour of the Wirick-Simmons house.

Watch the Christmas tree lighting, sing along with the Elizabeth Baptist choir while they sing Christmas carols around the Christmas tree, visit Santa at his grotto on East Dogwood Street, wander around the vendors on East Dogwood Street where there will be free balloon animals, face painting and crafts for the children, visit our downtown merchants for their Christmas specials and to participate in a scavenger hunt and raffle!

The scavenger hunt is fun, free and very easy to play! On the night of the event pick up a raffle

card from one of the participating merchants in town (they will have a flyer in the window), visit

each place listed on the card, the merchant will direct you as to what you will be looking for, find it, receive a stamp on your card and move onto the next place!

When your card is full just leave it with the last merchant you visit! Each completed card will be placed into a raffle to receive a gift certificate from one of the merchants on the card! There is no purchase necessary to play, you must be over 18 years of age to participate and only one card per family. You will be called if you are a lucky winner!!!
Come experience the spirit of a community Christmas in our small town of Monticello!

Monticello’s Downtown Community Christmas Event Vendor Information

Friday, December 1st from 5:00 pm to 8:00 pm.

The Community Christmas Tree will be set up in the Wirick-Simmons House back garden again and East Dogwood Street will be lined with vendors and Santa’s Grotto!
It is first come first serve for the booth space and location as well as the items you will be selling, homemade food, gift items or crafts. Vendor space is 6’ to 8’ wide, room for table, chair and a divider behind your booth to hang items. No Tents will be allowed due to the tight constrains of the area.

We would like to see all organizations and vendors raise money which is why we request that there are no duplicate items to be sold. At time of reservation we will let you know if another vendor is already selling the same or similar item.

I’m sorry, but there will be no food truck vendors for this event. Only fundraising not for profit vendors will be allowed to make and sell food to raise money for their organization**.

This year’s fee is $25.00 per spot for vendors. Please make your check payable to MAIN STREET MONTICELLO. The mailing address is: P.O. Box 923, Monticello, FL. 32345.

When we receive your check, it will mean that you agree to these guidelines. Once we receive your check you will be contacted and confirmed as a vendor!

Not for profit vendors will not be charged a fee.

There are some stipulations for the vendor requirements.

**There can be no open flames or cooking equipment that is in any way accessible to the public. Everything needs to be self-contained and in no way a fire hazard, must be isolated from the public and the right away. If it is deemed a fire hazard we will have to ask you to remove it

No tents allowed

No loud generators will be allowed.

You are responsible for your own table and chairs

•  Set up and clean up times must be adhered to. Set up time will be Friday December 1st, starting at 2:30 pm until 4:30 pm. All set up must be done no later than 4:30pm Clean up that same night cannot be done before 8:00pm Cars will not be allowed on the street at any time during set up or clean up.

We must have your check and acknowledgement of these guidelines by the deadline of November 22nd, 2017.

We appreciate you joining us for this year’s Monticello Downtown Community Christmas event!

For questions contact:
Joe Rosmini Main Street Vice President and Christmas Chair (772) 245-9076
Amy Rosmini Main Street Christmas Volunteer (772)359-3082 amy.rosmini@gmail.com


The Halloween Haunted Old Jail was a success!!
Fun was had by all. Next year in coordination with the downtown vendors we will expand on our success.

THANKS goes out to all of our volunteers and especially, the Monticello Fire Dept.



Main Street Mixers

Join us for our  quarterly Main Street mixers!  Good news, good food, good friends!
Mix and mingle!

Next Mixer to be held on October 19, 2017 at the Old Jail Museum.



Visit some of our
Historic Buildings

Avera Clarke House – Built in 1890, by Judge Thomas Clarke, is now a Bed and Breakfast owned by Gretchen and Troy Avera.

Constructed in 1885, Mr. T. M. Ferguson of Georgia. The Gothic style double Lancet windows hold stained glass windows made in England. The pews are made of solid pine, put together with wooden pegs. The Rev. James Bowen May is the current Rector.

Built in 1890 by Monticello businessman John H. Perkins. The Monticello Opera House is commonly used for a variety of events including children’s theater, murder mystery dinners and large musicals. There is also a patio and gazebo in the back where weddings and receptions are held.

Old Jail

The Masonry Vernacular building was constructed in 1909, with alterations in 1940 and 1960. The design is typical for small jails of the early twentieth century: on the first floor there are the living quarters for the sheriff or deputy and his family, and on the second floor there are the steel cages for the inmates. It is one of only two standing buildings of this design left in the U.S. It was added to the National Register of Historic Places on January 15, 2014.

Built in 1909, it was designed by Georgia-born American architect Edward Columbus Hosford, who is noted for the courthouses and other buildings that he designed in Florida, Georgia and Texas. It was added to the National Register of Historic Places on August 19, 1977



For more about Monticello visit: www.visitjeffersoncountyflorida.com.